Compare Vacation Rentals & Airbnb in Oakville

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Oakville vacation rentals
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871 Rentals and Airbnb in Oakville

Best family friendly Oakville vacation rentals

Among the 871 accommodations in Oakville, here are the 4 best family friendly rentals

Luxury-5 Br-king Bed-2 Car-pond View-403/407/qew - Oakville
9.8 79 reviews

Luxury-5 Br-king Bed-2 Car-pond View-403/407/qew

apartment, Milton
This five-bedroom house, near the junction of the 403, 407 and QEW motorways, is situated approximately 10 km from Oakville GO station and within 8 km of shops including Walmart and Longo's supermarket in Oakville.
Offering self-check-in, this spacious property sleeps 12 guests and boasts a modern kitchen with dishwasher, two workspaces, a garden, parking, and ultra-high-speed internet (1 Gbps), plus two Smart TVs.
Modern Townhouse Rooftop Vibes - Oakville
No reviews

Modern Townhouse Rooftop Vibes

house, Milton
This Milton house, sleeping seven guests, offers one bedroom and three bathrooms within an 111 square metre space and includes free private parking; its precise location within Milton requires further clarification to determine proximity to local landmarks.
The property boasts a fully equipped kitchen, free Wi-Fi, a terrace/balcony, air conditioning, and an outdoor fireplace, perfect for relaxing evenings.
Sun-kissed 3br Family Home In A Quiet Neighborhood - Oakville
9.9 126 reviews

Sun-kissed 3br Family Home In A Quiet Neighborhood

apartment, Toronto
This spacious home is located in Oakville, a suburb 30 kilometres west of Toronto, and is close to Sheridan College, Walmart, Oakville Place mall, and the lakeshore. The property enjoys excellent user, location, and cleanliness ratings.
The detached house offers 3 bedrooms and 1.5 bathrooms, comfortably accommodating up to 6 guests. The house is fully equipped with a modern kitchen, a large garden, high-speed internet, free parking, and automated check-in and check-out.
Luxury Apartment Living - Oakville
8.8 22 reviews

Luxury Apartment Living

apartment, Toronto
This Mississauga apartment, situated approximately 24 kilometres from Toronto Pearson International Airport and 24 kilometres from the Mississauga Convention Centre, offers convenient access to major attractions.
The self-catering flat comprises one bedroom, one bathroom, and accommodates up to five guests, featuring a private garden, free parking, Wi-Fi, and air conditioning.

Best Oakville vacation rentals with parking

Luxury Retreat In Top Location - Oakville
9.6 64 reviews

Luxury Retreat In Top Location

apartment, Milton
This excellent, family-friendly basement flat in a prestigious Milton neighbourhood is conveniently located near the GO station, Walmart, and Canadian Superstore.
The two-bedroom, one-bathroom self-catering apartment sleeps five, boasts a fully equipped kitchen including a dishwasher, high-speed Wi-Fi, Netflix, and parking, offering comfortable accommodation near Lakeshore and Milton town centre.
Modern Private 1-bed Suite | Parking | Oakville - Oakville
10 3 reviews

Modern Private 1-bed Suite | Parking | Oakville

apartment, Toronto
This Oakville basement flat, located in a quiet residential area, provides convenient access to public transport with Bronte GO just a few minutes walk away, placing Downtown Toronto approximately 56 kilometres distant and Niagara Falls about 1 hour away by car.
This one-bedroom, one-bathroom flat accommodates two guests and offers high-speed Wi-Fi, air conditioning, free parking, a kitchen equipped with a fridge, freezer, and microwave, and a dedicated workspace, ideal for those visiting the Toronto area.
Lakeside Luxury: Escape To Our Stunning Retreat! - Oakville
9.7 86 reviews

Lakeside Luxury: Escape To Our Stunning Retreat!

apartment, Toronto
This one-bedroom apartment is situated in Bronte, Oakville, a lakeside district just 32 kilometres southwest of Toronto city centre, offering easy access to both the tranquil waterfront and the city's attractions.
The self-contained flat features a fully equipped kitchen, a cosy fireplace, a dedicated workspace, and a private entrance, comfortably accommodating up to three guests.
Tim Allen's Santa Clause House - Oakville
10 1 review

Tim Allen's Santa Clause House

apartment
This luxurious Oakville townhouse, a former filming location for 'The Santa Clause', is situated close to Lake Ontario, offering scenic views and convenient access to local attractions.
The two-bedroom, two-bathroom property sleeps four guests and boasts a modern kitchen, fitness centre, and on-site yoga studio, celebrating the film's 30th anniversary with a unique holiday experience.

Frequently Asked Questions about vacation rentals in Oakville

  • What should a first-time visitor not miss in Oakville?

    Oakville has a lot to offer, but for a first-timer, you shouldn't miss the waterfront. Stroll along the Oakville Harbour, visit the Oakville Museum, and maybe catch a show at the Oakville Centre for the Performing Arts.
  • What are the best Airbnb and vacation rentals in Oakville?

    Waterfront Coach House Loft, The Wine Cellar and Cozy 2 Bedroom Basement Apartment are the most popular Airbnb and vacation rentals in Oakville among travelers.

  • Which neighborhood in Oakville should you consider for a vacation rental?

    For a vacation rental, you might want to consider the Old Oakville neighbourhood. It's charming, with historic buildings and a vibrant atmosphere, and it's close to the waterfront and shops.
  • What are the most popular Airbnbs in Oakville?

    Among the Airbnbs in Oakville, Waterfront Coach House Loft, The Wine Cellar and Cozy 2 Bedroom Basement Apartment are the most popular ones.

  • What are the top family-friendly attractions in Oakville?

    For families, the Oakville Museum is a great place to start. Kids will love the hands-on exhibits, and the museum's location on the waterfront makes it even more appealing. Also, the Oakville Public Library is a great place to visit with children, with a variety of programs and events.
  • What are the best vacation rentals with a pool in Oakville?

  • When is the best time to book a vacation rental in Oakville?

    The best time to book a vacation rental in Oakville depends on your preferences. If you want to experience the summer festivals and outdoor activities, July and August are ideal. However, for a quieter getaway, spring or autumn might be better.
  • What are the best rentals for families and kids in Oakville?

    The best rentals for families and kids in Oakville are Home Away From Home (Basement Apartment), Pathway Suites and Cozy & Beautiful Basement Apartment.

  • What events or festivals should visitors check out in and around Oakville?

    Oakville has a lively events calendar throughout the year. The Oakville Jazz Festival in July is a popular event, and the Oakville Fall Fair in September is a great family-friendly event. You could also check out the Bronte Creek Provincial Park for events.
  • What are the best rentals or Airbnbs with a jacuzzi in Oakville?

    The best vacation rentals or Airbnb with a jacuzzi in Oakville are Pathway Suites, Beautiful Cozy 1 Br Condo Steps To Sq1 and Luxurious1 Br Condo In Downtown Mississauga .

  • What are the best budget-friendly activities in Oakville?

    Oakville has plenty of free and budget-friendly activities. A walk along the waterfront is always enjoyable, and you can explore the many parks and green spaces. You can also visit the Oakville Public Library, which offers free events and programs.
  • What are the best restaurants with local dishes in Oakville?

    For local dishes, try the Oakville Fish Market for fresh seafood, or The Oakville Chop House for a classic Canadian steakhouse experience. For something a bit more casual, The Oakville Brewing Company serves up delicious pub fare.
  • What are the best walking or cycling routes in Oakville?

    The Waterfront Trail is a popular choice for walking and cycling, offering scenic views of Lake Ontario. The Oakville Creek Trail is another great option, winding through the town's natural areas. You can also check out the trails at Bronte Creek Provincial Park.
  • Are there pet-friendly attractions in Oakville?

    Many parks and green spaces in Oakville are pet-friendly, including the Oakville Harbour. You can also find dog-friendly patios at some restaurants and cafes.
  • What are the benefits of choosing a vacation rental in Oakville?

    Vacation rentals offer more space and privacy compared to hotels. They often come with amenities like kitchens and laundry facilities, which can be convenient for families or longer stays. They can also be a more affordable option, especially for larger groups.
  • What are the top sports attractions and facilities in Oakville?

    Oakville has several sports facilities, including the Oakville Soccer Club, the Oakville Tennis Club, and the Oakville Golf Club. The town also hosts a variety of sporting events throughout the year.

Popular destinations

Best Oakville vacation rentals with a balcony

Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville - Oakville
No reviews

Royal Stays Townhome Collection - 3 Bedroom Townhome In Oakville

apartment, Milton
This 3-bedroom townhouse is located in Oakville, just 27 kilometres from Mississauga Convention Centre and Toronto Pearson International Airport, and 37 kilometres from BMO Field and Budweiser Stage. The property enjoys excellent location and cleanliness ratings, with guests consistently praising its comfort and convenience.
The townhouse offers 172 square metres of space, comfortably accommodating up to 6 guests. A fully equipped kitchen, private terrace, air conditioning, free Wi-Fi, satellite TV, and parking are all provided for your enjoyment.
Modern Luxury Townhome With 2br Balcony Plus Parking - Happy Oaks - Oakville
10 2 reviews

Modern Luxury Townhome With 2br Balcony Plus Parking - Happy Oaks

house, Toronto
This modern luxe residence is situated in Oakville, 26 kilometres from the Mississauga Convention Centre and 32-35 kilometres from Toronto landmarks such as BMO Field, Rogers Centre, and the CN Tower, with Toronto Pearson International Airport located 26 kilometres away.
This property offers free WiFi, private parking, air conditioning, a kitchen, and a balcony, accommodating up to seven guests with a check-out time of 11:00 AM.
Modern Luxury Home Near Bronte Harbour & Oakville Downtown - Oakville
No reviews

Modern Luxury Home Near Bronte Harbour & Oakville Downtown

house, Toronto
This spacious five-bedroom detached house is situated in Oakville, offering a peaceful setting 37 kilometres from the Mississauga Convention Centre and 42 kilometres from BMO Field, with the marina a mere 720 metres walk away.
The property boasts 19 square metres of floor area, accommodates up to 27 guests, and features a fully equipped kitchen, a fireplace, an indoor play area, a balcony, a garden, private parking, and free WiFi.
Entire Home In Oakville, Canada - Oakville
9.0 3 reviews

Entire Home In Oakville, Canada

house, Hamilton
This Oakville property, situated approximately 29 kilometres from Toronto Pearson International Airport and within a 39-kilometre radius of attractions such as BMO Field and Exhibition Place, offers a convenient base for exploring both Hamilton and Toronto.
This three-bathroom house sleeps fifteen guests, boasting a fully equipped kitchen, free Wi-Fi, private parking, and a balcony; nearby activities include exploring Oakville's suburban attractions.

Best Oakville vacation rentals with air conditioning

Serene Oakville Retreat - Modern 2-bedroom Apartment - Oakville
No reviews

Serene Oakville Retreat - Modern 2-bedroom Apartment

apartment, Milton
This two-bedroom flat is situated in Halton, offering convenient access to Oakville (32 kilometres), Mississauga (32 kilometres), and Toronto (56-77 kilometres), with a GO Station a mere 7-minute drive away.
This family-friendly apartment, accommodating up to four guests, boasts a fully equipped kitchen, air conditioning, a jacuzzi, and private parking, and is located within a 15-minute drive of Oakville Place, Toronto Premium Outlet, and Erin Mills Town Centre.
Modern 2-bed Basement Retreat! - Oakville
9.4 3 reviews

Modern 2-bed Basement Retreat!

apartment, Toronto
This Erin Mills holiday home in Toronto is conveniently located within 3km of Woodhurst Heights Park, the Erin Mills Twin Arenas, and the Oakville Entertainment Centre.
This two-bedroom, two-bathroom property sleeps five, offering a fully equipped kitchen, free Wi-Fi, a smart TV, and parking; nearby attractions include Putting Edge and iFLY Toronto Oakville (within 5km).
Brand New Condo-bed+sofa Bed Bright Unit+parking - Oakville
9.5 11 reviews

Brand New Condo-bed+sofa Bed Bright Unit+parking

apartment, Milton
This one-bedroom flat is located in a central Milton district, providing easy access to local amenities.
This flat accommodates up to three guests and includes essential amenities such as air conditioning, a kitchen, and parking, making it ideal for both business and leisure stays.
Spacious And Luxurious 2br Suite With Huge Windows - Oakville
8.7 3 reviews

Spacious And Luxurious 2br Suite With Huge Windows

apartment, Toronto
This Mississauga apartment, situated 19 kilometres from Toronto's downtown attractions including the BMO Field and Exhibition Place, offers convenient access to both the city and Pearson International Airport (18 kilometres).
This two-bedroom, two-bathroom flat boasts 46 square metres of space, comfortably accommodating up to nine guests and featuring free parking, Wi-Fi, and a fully equipped kitchen.
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